Recipe: Acorn Squash Stuffed with Bread, Cheese, and Bacon

I have Dorie Greenspan to thank for this recipe. Last year, I wrote about her Pumpkin Filled with Bread and Cheese, a recipe I've since seen updated in Fine Cooking. Thing is, I'd rather eat squash than pumpkin — and I only needed to feed two people. So I swapped out the pumpkin for a more modestly sized acorn squash, along with a few other tweaks, to make this into a weeknight meal — including an all-important step for getting that delicious, caramelized crust on top!

Acorn squash was the obvious choice for downsizing Dorie's recipe, but it had one problem: Dorie puts the cap back on her pumpkin after filling it with bread, cheese, and cream, so she had a little oven-within-an-oven.

I wanted to slice the acorn squash in half instead and leave the stuffing exposed. After a bit of trial and error, I finally figured out this awesome trick: Bake the stuffed squash upside-down, just like you would if you were roasting it. The heat gets trapped and the hard squash cooks much, much faster. The bonus? The filling, which is smashed down against the bottom of the dish, caramelizes on its surface to form a crunchy, brown crust — the perfect texture to go with the soft squash and gooey cheese.

With its nice bowl shape, the squash-to-filling ratio also ended up being just right. This is one experimental dinner that is definitely going into regular rotation.

Tester's Notes

This is the stuffed squash that made me step outside of my stuffed squash comfort zone. Until now my stuffed squashes have been kind of weak. Without fail, I almost always end up stuffing them with some version of wild rice or quinoa, and a mix of leafy greens, mushrooms, dried fruit, and maybe some crunchy nuts. Never in my wildest dreams did I consider a filling that mixed bacon, shallots, bread, and cheese — it's comforting, cozy and supremely satisfying.

Baking the squash cut-side down is a total game changer, as well. The top layer of the filling is wonderfully crispy and crunchy, and the surface of the squash takes on a rich, caramelized flavor.

The medium size of acorn squash gives this dish the versatility to play main course or side dish (albeit, a very filling one). If you're making this as a main course I suggest including something a little extra, like a nice salad or small bowl of soup.

Cook the bacon in a skillet over medium heat until crispy. Remove, crumble, and set aside. In the same pan, cook the shallot until beginning to brown, about 4 to 5 minutes. Add the garlic and sage and cook just until fragrant, about one minute (don't burn the garlic).

In a medium bowl, combine the shallot mixture, bread cubes, cheese, and bacon. Pour in the cream and stir until everything is moistened. Add 1/2 teaspoon of salt and a few grinds of pepper.

Rub a little olive oil into the squash, coating the sliced edges and the cavity. Sprinkle over some salt and pepper. Divide the stuffing between the halves, packing it in so that the squash can still lie flat when turned upside-down.

→ At this point, the stuffed squash halves can be refrigerated for up to 24 hours before cooking. Add 5 to 10 minutes to the total cooking time.

Carefully place the squash halves upside-down in a baking dish. Bake for about one hour, until the flesh of the squash can be easily pierced with a knife. If the juices and cheeses start to burn after 30 or 45 minutes, add a few tablespoons of water to the dish. Once the squash is cooked, use a spatula (or two) to flip them over. Serve as is or slice down the middle.

Recipes Notes:

The inside pocket of each squash will be a little different. Mine was quite small, so I scooped out a little extra flesh to make room for all of the stuffing.